Venture Capital

The practice of investing capital in early-stage companies with high growth potential, including fund management and startup evaluation.

21 episodes

Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52

Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52

Steve Walsh, an angel investor and startup advisor, shares lessons from 25 years building multi-billion dollar B2B divisions at Cox and Comcast before transitioning to helping early-stage founders. He discusses common founder mistakes, when to raise capital, the importance of customer validation before building product, and how he filters 6,000 conversations down to 69 investments through rigorous vetting and founder education.

If You're Not Making Money, You're Not Worth Money: 1,000 Valuations | Gregg Ficery, Ep 51

If You're Not Making Money, You're Not Worth Money: 1,000 Valuations | Gregg Ficery, Ep 51

Gregg Ficery, founder of Integgra Advisory Services, discusses his 15-year career in business valuation, explaining when companies need valuations (fundraising, 409A compliance, M&A, litigation), how to maximize company value, and current trends in venture capital and AI investment. He shares his journey from dot-com survivor to Silicon Valley Bank to independent consultant, plus his side project: a book documenting pre-NFL professional football history.

What Builders Get Wrong About Capital, From Someone Who Knows Both Sides | Kumar Ampapathini, Ep 48

What Builders Get Wrong About Capital, From Someone Who Knows Both Sides | Kumar Ampapathini, Ep 48

Kumar Ampapathini, a fractional CFO and former Wall Street banker, discusses his transition from software engineering at Cisco to investment banking and eventually fractional CFO work. He explains how AI is transforming startup economics, why institutional investors prioritize path-to-profitability over pure growth, and what founders misunderstand about capital. Kumar shares M&A negotiation insights and emphasizes that strong founders matter more than perfect products.

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Chris Thomajan, a CFO with 35 years of experience across 100+ startups, discusses his career path from English major to finance leader in Boston's biotech ecosystem. He shares frameworks for evaluating founding teams, navigating venture capital cycles, and preparing companies for IPO, emphasizing that betting on the right 'jockey' matters more than the business idea itself.

2026 Trends: Trust in AI, Healthcare, College, AGI & More | Bryan Dennstedt, Ep 41

2026 Trends: Trust in AI, Healthcare, College, AGI & More | Bryan Dennstedt, Ep 41

Todd and Bryan Dennstedt review their 2025 AI predictions, finding they accurately forecasted the AI trough of disillusionment, agentic AI emergence, and VC conservatism. They predict 2026 will be defined by organizational absorption of AI capabilities rather than new breakthroughs, with agentic workflows becoming default, SaaS pricing models compressing, and trust verification emerging as a critical business category. They emphasize that rapid AI-powered software development is fundamentally changing startup economics and making previously marginal business ideas viable.

Business Model First, Product Second: Thirty Years of Building Smarter | Steve Subar, Ep 40

Business Model First, Product Second: Thirty Years of Building Smarter | Steve Subar, Ep 40

Steve Subar, serial entrepreneur and inventor of MatFresher, discusses his business-model-first approach to building companies. After 30+ years founding and exiting ventures including Open Kernel Labs (acquired by General Dynamics), Subar explains how he validated product-market fit for MatFresher—an automated yoga mat cleaning machine—by manually cleaning mats at studios before building the product. He emphasizes innovating business models alongside technology, the importance of experience over information, and why wisdom beats rapid iteration.

Decades of Financial Strategy Across 70 Companies and Still Going | Neal Miller, Ep 39

Decades of Financial Strategy Across 70 Companies and Still Going | Neal Miller, Ep 39

Neil Miller, a partner emeritus at Tech CXO with nearly 20 years of fractional CFO experience across 70+ companies, shares his career journey from public accounting through multiple CFO roles at public companies to pioneering fractional executive work. He discusses value creation stories including Cloud Sherpas (acquired by Accenture) and Boomtown (90M+ revenue exit), the current venture capital environment, and how AI tools are compressing startup development cycles while raising the bar for execution speed.

The 5-Hour Workday: Maximum Productivity in Minimal Time | Alex Gafford, Ep 33

The 5-Hour Workday: Maximum Productivity in Minimal Time | Alex Gafford, Ep 33

Alex Gafford, a corporate finance executive at Blue Street Capital, discusses his company's nine-year experiment with a five-hour workday that increased productivity by 24% and revenue by 30%. He explains how condensed work schedules, protected focus time, and AI tools enable knowledge workers to achieve peak performance while maintaining work-life balance, challenging traditional assumptions about hours worked versus results delivered.

From Pink Slip to Pivot: Predictable Sales in Unpredictable Markets | Joe Gruca, Ep 32

From Pink Slip to Pivot: Predictable Sales in Unpredictable Markets | Joe Gruca, Ep 32

Joe Gruca, newly joined partner at Tech CXO, shares his journey from corporate VP of Sales through founding Higher IQ (an AI-powered interview platform acquired after raising venture capital) to fractional revenue leadership. He discusses navigating the 2008 financial crisis as an accidental entrepreneur, building predictable sales motions for early-stage B2B SaaS companies, and how AI is transforming both sales execution and customer success while the fundamentals of relationship-building remain constant.

Beyond Resumes: The Case for Talent-First, Human-Centered Hiring | Teja Yenamandra, Ep 29

Beyond Resumes: The Case for Talent-First, Human-Centered Hiring | Teja Yenamandra, Ep 29

Teja Yenamandra, founder of Gun.io, discusses building a talent-first freelance marketplace that connects senior software engineers with companies based on merit rather than price. He shares insights on remote work culture, AI's impact on software development, the importance of relationship-focused venture capital partnerships, and how the developer job market is shifting toward backend and AI implementation work.

Tariffs and Economic Uncertainty: How We Got Here and What's Next | Michael Weinstein, Ep 28

Tariffs and Economic Uncertainty: How We Got Here and What's Next | Michael Weinstein, Ep 28

Michael Weinstein, a fractional CFO with decades of Wall Street and corporate finance experience, analyzes the current economic uncertainty driven by tariff policy, Federal Reserve decisions, and structural market challenges. He explains how tariffs function as a massive tax increase, why venture capital liquidity has frozen, and how uncertainty prevents corporate investment—while arguing that entrepreneurship and new business formation will ultimately lead the economy out of stagnation.

The Rise of Agentic Systems and AI-Driven Development | Jeff Haynie, Ep 27

The Rise of Agentic Systems and AI-Driven Development | Jeff Haynie, Ep 27

Jeff Haynie, serial entrepreneur and founder of Appcelerator (acquired after reaching 1M+ developers), discusses his journey from building cross-platform mobile frameworks in 2006 to launching Agentuity, a cloud platform for AI agents. He shares lessons from raising capital in Silicon Valley, navigating acquisitions, and why he believes agentic systems will require fundamentally different infrastructure than today's human-centric cloud.

Earning Every Win: Grit, Innovation, and Knowing When to Venture | Lisa Calhoun, Ep 25

Earning Every Win: Grit, Innovation, and Knowing When to Venture | Lisa Calhoun, Ep 25

Lisa Calhoun, managing partner of Valor Ventures, discusses her fourth-generation entrepreneurial background and leading seed-stage B2B AI and SaaS investments across the South. She explains venture capital's relational nature, the 2024 venture winter that shuttered 40% of smaller funds, and how AI is eliminating coding as a constrained resource while transforming software development economics.

2025 Trends: AI, Venture Capital, and the Future of Work | Bryan Dennstedt, Ep 22

2025 Trends: AI, Venture Capital, and the Future of Work | Bryan Dennstedt, Ep 22

Bryan Dennstedt, fractional CTO at Tech CXO and sustainable investing advocate, discusses 2025 trends with host Todd. They cover venture capital's conservative shift post-SVB, AI's permeation across business (from agents to trust frameworks), the rise of niche podcasts and influencer marketing, and crypto's regulatory thaw under new US leadership. Core insight: AI and blockchain will become as fundamental as electricity, but organizations must navigate trust, compliance, and the trough of disillusionment before realizing transformative value.

Triathlons, Startups, and Success: A Playbook for Entrepreneurs | Kathryn O'Day, Ep 19

Triathlons, Startups, and Success: A Playbook for Entrepreneurs | Kathryn O'Day, Ep 19

Katherine O'Day, partner at Atlanta Ventures, discusses her journey from employee number nine at Pardot through two successful acquisitions (ExactTarget, then Salesforce) to becoming an early-stage investor and venture studio operator. She shares lessons on bootstrapping companies, building culture through core values, and why consistent execution over time—like training for an Ironman—matters more than short bursts of effort in entrepreneurship.

Mastering UK-US Market Entry from Either Side of the Pond | Marc McCarthy, Ep 13

Mastering UK-US Market Entry from Either Side of the Pond | Marc McCarthy, Ep 13

Marc McCarthy, founder of Pro Consult IQ, discusses the complexities of B2B software expansion between UK and US markets. He covers cultural sales differences, regulatory considerations across US states, the importance of hiring locally, and strategic decisions around partnerships versus direct market entry. McCarthy emphasizes that shared language creates false assumptions about ease of expansion, and successful cross-Atlantic growth requires understanding time zones, legal frameworks, pricing strategies, and customer expectations that differ significantly between markets.

Hard-Won Lessons from a Long and Successful Tech Journey | Chris Caparon, Ep 10

Hard-Won Lessons from a Long and Successful Tech Journey | Chris Caparon, Ep 10

Chris Caparon, co-founder and former CEO of Sephoria Software, shares his 20-year journey building an accounts receivable automation company from a garage startup to a successful exit to private equity. He discusses navigating multiple economic crises, evolving technology platforms, and the relentless customer focus that enabled his bootstrapped company to serve Fortune 500 clients across 110 countries.

Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success | David Morczinek, Ep 08

Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success | David Morczinek, Ep 08

David Morczinek, CEO of Airworks, discusses his journey from aerospace engineering at Airbus to founding a geospatial AI company at MIT. He explains how Airworks analyzes aerial data from drones, satellites, and aircraft to automate infrastructure mapping, the pivot from pure AI to AI-plus-services when customers weren't ready for full automation, and navigating multiple funding rounds from seed to private equity while maintaining work-life balance.

Cultivating Resilience Through Adaptation, Partnership and Growth | Christy Johnson, Ep 07

Cultivating Resilience Through Adaptation, Partnership and Growth | Christy Johnson, Ep 07

Christy Johnson, performance engineering lead at VIP Ventures, discusses her unconventional path from microfinance in Costa Rica to steel manufacturing to venture capital. She shares lessons from seven years as CEO of a portfolio company, the importance of culture in remote teams, and VIP's hands-on approach to helping founders through focused strategy, investor symposiums, and operational coaching.

A Journey Through Valuations, Ventures, Visions and Vodka | Mike Blake, Ep 06

A Journey Through Valuations, Ventures, Visions and Vodka | Mike Blake, Ep 06

Mike Blake, founder of High Score Strategies, discusses business valuation methodology, the changing landscape of patent protection, and his journey from venture capital to running a valuation consultancy from Portugal. He shares insights on helping founders navigate term sheets, the limitations of valuation in early-stage negotiations, and the story of launching Atlanta's Startup Lounge networking events that helped build the city's entrepreneurial ecosystem.

From Rowing to Venture Capital: Lessons in Teamwork and Growth | Mark Flickinger, Ep 04

From Rowing to Venture Capital: Lessons in Teamwork and Growth | Mark Flickinger, Ep 04

Mark Flickinger, partner at BIP Ventures, discusses his journey from mechanical engineering and competitive rowing to venture capital. He explains BIP's platform-heavy approach to supporting portfolio companies, the firm's focus on high-net-worth investors, and strategies for navigating the current venture market. Flickinger emphasizes the importance of board governance, team-based competitive experience, and building sustainable businesses during economic downturns.

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